Monohalophenylthiazolyl ureas



Patented Mar. 10, 1970 3,499,910 MONOHALOPHENYLTHIAZOLYL UREAS Patrick Robert Driscoll, Fords, N.J., assignor to Mobil Oil Corporation, a corporation of New York No Drawing. Filed May 8, 1967, Ser. No. 636,589 Int. Cl. C07d 91/34; A0111 9/22 US. Cl. 260306.8 1 Claim ABSTRACT OF THE DISCLOSURE Monohalophenylthiazolyl ureas are new compounds that are effective for the control of plant parasitic nematodes and are not phytotoxic to plants. A particularly effective material is 1-methyl-3-[4-(p-chlorophenyl)-2- thiazolyl] urea.

BACKGROUND OF THE INVENTION Field of the invention This invention relates to the control of plant-parasitic nematodes. It is more particularly concerned with certain thiazolyl ureas and their use in controlling nematodes.

DESCRIPTION OF THE PRIOR ART The use of chemicals for nematode control is a comparatively recent development. In view of the complex structure of the nematode, experimental approaches which could lead to effective toxicants have been difficult. The nematodes, as well as the egg thereof, is protected by a difficulty permeable membrane, and the effective toxicant must have the ability to penetrate this membrane and the ability to kill. Toxicants must also be readily dispersible in soils or other environment of the organism and be stable therein. Since the reason for ridding soils of nematode infestations is to provide a beneficial growing media for plants, the nematocide must be non-phytotoxic to plants, or its phytotoxicity must be short-lived. A phytotoxic nematocide, either itself or some decomposition product of it, should be such that, prior to crop planting, it is removed from the soil by evaporation, by rain washing, or by soil bacterial action.

Various chemicals have been proposed for the control of nematocides. For example contact nematocides have been developed from certain phosphorous esters (US. 3,112,244). Insofar as is now known, urea derivatives have not been proposed as nematocides.

SUMMARY OF THE INVENTION This invention provides the compound having the formula:

DESCRIPTION OF SPECIFIC EMBODIMENTS The compounds utilizable in accordance with this invention are compounds having the structure --N t an wherein x is halogen and R is lower alkyl (C -C Non limiting examples of the compounds of this invention are:

1-methyl-3-[4-(p-chlorophenyl)-2-thiazolyl] urea, l-mcthyl-3- [4- o-chlorophenyl) -2-thiazolyl] urea, 1 -methyl-3- [4- (m-chlorophenyl) -2-thiazolyl] urea, l -methyl-3- [4- (p-bromophenyl) -2-thiazolyl] urea, 1-isobutyl-3- [4- (p-bromophenyl -2thiazolyl] urea, l-isobutyl-3- [4 (p-chlorophenyl) -2-thiazolyl] urea, l-propyl-3- [4- (p-chlorophenyl) -2-thiazolyl] urea, l-methyl-3- [4- (o-iodophenyl -2-thiazolyl] urea, 1-methyl-3- [4- (m-iodophenyl) -2-thiazolyl] urea, 1-methyl-3-[4-(m-bromophenyl)-2-thiazolyl] urea, and 1-ethyl-3- [4- (p-chlorophenyl) -2-thiazolyl] urea.

These compounds can be prepared by several methods known in the art, but it must be strictly understood that this invention is not limited by the manner in which the compounds are prepared. As is demonstrated in the specific examples a feasible method is first to react a ringhalogenated acetophenone, thiourea and iodine to obtain a 2-amino-4-halophenyl thiazole. This is then reacted with methyl isocyanate to produce the thiazolyl urea.

In carrying out the method of this invention for controlling nematodes the chemicals of this invention can be applied in various ways. They are usually applied to the soil as the toxic components in a nematocidal composition comprising a nematocidal amount of the nematocide and a carrier for a nematocide. Such compositions can be applied as dust or as liquid sprays. In addition to the carrier they can contain additives such as emulsifying agents, wetting agents, binding agents, odorants and stabilizers. Liquid and solid carriers known for nematocides include water, organic solvents, mineral oils, clays, and ground walnut sheels.

The exact quantity of the compounds of this invention to be utilized in nematocidal compositions will be found to vary somewhat. It depends to some extent on the type of composition in which the material is being employed, the method of application and the severity of the condition to be controlled. In practice nematocidal application is measured in terms of pounds of nematocide applied per acre. The compounds of this invention are effective when applied in nematocidal amounts, i.e., at rates between about one pound and about 20 pounds per acre, preferably at about 3 to 10' pounds per acre.

Application of the chemicals of this invention to foodcrop land priorto planting is preferable, one reason being that it is less difficult to treat a field wherein no crops are growing. Prior treatment can in no way reduce the length of the growing season, for the chemicals are not phytotoxic when used in nematocidal amounts. Crops can, therefore, be planted immediately after treatment if desired. This is very important, especially in some zones wherein the growing season is relatively short and any method for nematode control which tends to shorten the growing season cannot be tolerated.

EXAMPLE 1 2-amino-4-(p-chlorophenyl) thiazole p-Chloroacetophenone (40.0 g., 0.26 mole), thiourea (39.3 g., 0.52 mole) and iodine (65.8 g., 0.26 mole) were mixed together and heated on a steam bath for 16 hours. The mixture was cooled, washed well with etherand filtered. The crude solid was slurried with 600 ml. of hot water and neutralized with concentrated NH OH. The neutralized solid was filtered and recrystallized from ethanol, M.P. -64".

Analysis.Calcd (percent): C, 51.30; H, 3.35; N, 13.30. Found (percent): C, 51.55; H, 3.68; N, 13.02.

3 EXAMPLE 2 1-methyl-3- [4- (p-chlorophenyl -2-thiazolyl] urea NEMATOCIDAL TEST Method of rearing root-knot nematodes Root-knot nematode (Meloidogyne incagnita) cultures are maintained in the greenhouse in 7 clay pots using tomato, var. Rutgers, as the host plant. Two 8-week old pots of infested soil are used to inoculate 72 three-inch pots of noninfested soil in the cement mixer for minutes. Two 7" pots of this mixture are returned to the greenhouse for future tests.

Method of treatment One hundred mg. of test compound is weighed on the analytical balance and formulated using 1 ml. of Tween 20, 9 ml. of acetone and 90 ml. of water. Four ml. and 81 ml. aliquots are diluted to 50 ml. with water for the 10 and 20 lb. active per acre rates. The 50 ml. of formulation is poured over soil sufiicient for three 3" pots, stirred into the soil with a hand fork and placed in the pots. The pots are buried to the lip in the greenhouse sand bench. After 24 hours, 5 cucumber seeds, variety Early Fortune, are planted in each pot.

Method of recording results After 4 weeks, the plants are rated for phytotoxicity and the roots removed from the pots and rated for rootknot control based on the degree of root galling.

The compound of example 2 was subjected to the nematocidal test at application rates of 20 and of 10 pounds per acre. At 20 pounds per acre 100% control was achieved. At 10 pounds per acre control was achieved. At both dosages this material was not phytotoxic.

Although the present invention has been described with preferred embodiments, it is to be understood that modifications and variations may be restorted to, without departing from the spirit and scope of this invention, as those skilled in the art will readily understand.

What is claimed is:

1. 1-methyl-3-[4-(p-chlorophenyl)-2-thiazolyl] urea.

References Cited Beyer et al., Chem. Abstracts, vol. 65, col. 18572c, Dec. 5, 1966.

ALEX MAZEL, Primary Examiner R. J. GALLAGHER, Assistant Examiner US. Cl. X.R. 424-270 (5/69) UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3, +99,9l Dated March 10, 1970 Invent'm-(S) PATRICK ROBERT DRISCOLL It is certified that error appears in the aboveidentified patent and that said Letters Patent are hereby corrected as shown below:

Col. 3, Line 3O, "81 ml" should be --8 ml-- SIGNED AND SEALED JUL 1 4197B Edward M. Fletcher, In Amsfing Officer WILLIAM E. SW, m.

Gomissioner of Pawn" 

